ZA200202082B

ZA200202082B - Fungicides.

Info

Publication number: ZA200202082B
Application number: ZA200202082A
Authority: ZA
Inventors: Norman John De Ath; John Klostermyer
Original assignee: Aventis Cropscience Gmbh
Priority date: 1999-09-17
Filing date: 2002-03-13
Publication date: 2003-08-27
Also published as: DE60008253D1; JP2003509514A; DE60008253T2; EP1212332B1; EA200200373A1; AU780952B2; PL192383B1; HRP20020337A2; KR100695637B1; UA71998C2; MXPA02002850A; GB9921930D0; HRP20020337B1; HUP0202777A2; MA25502A1; IL148574A; ATE259367T1; CA2384027A1; AR029003A1; HUP0202777A3

Description

\ . - ya " * : 1 . Title: Fungicides . - This invention relates to a new compound having fungicidal activity. 5. . - In one aspect, the invention provides a compound of formula | :

OA+ : @ Jumma 1 )] : - OA+

N “where X is hydrogen or O"A* and A is a radical 0]

NTN J

~~ N N 0 ~~ 10.. The two compounds resulting are dimethyl-[3-(propoxycarbonylamino)propyl]- § ammonium phosphate and dimethyi-[3-(propoxycarbonylamino)propyllammonium ; - phosphite BREA

The compounds of the invention have activity as fungicides, especially against 15. Phycomycete diseases of plants. e.g. vine downy mildew (Plasmopara viticola), various Phytophthora blights e.g. late tomato or potato blight (Phytophthora infestans),

Pythium spp., Aphanomyces spp:, Bremia spp.. Perenospora spp. and

Pseudoperenospora spp.

The invention thus also provides a method of combating fungi at a locus infested or : Co "liable to be infested therewith, which comprises applying to the locus the compounds of the invention. : The invention also provides an agricultural composition comprising the compounds of the invention in admixture with an agriculturally acceptable diluent or carrier.

The composition can comprise one or more additional active ingredients, for example compounds known to possess plant-growth regulant. herbicidal. fungicidal, insecticidal

' . or acaricidal properties. Alternatively the compound of the invention can be used in sequence with the other active ingredient.

Fungicides with which the compound can be mixed include acylanilines, such as metalaxyl, oxadixyl, ofurace, benalaxyl and furalaxyi; cymoxanil; mancozeb; chiorothalonil; folpet; captan; famoxadone; fenamidone; spiroxamine; fluazinam; dimethomorph; strobilurins, such as kresoxim-methyl, azoxystrobin and trifloxystrobin, pyrimethanil, cyprodinil; mepanipyrim; and iprodione.

The names quoted for these compounds are the non-proprietary common names and Co the chemical structure can be found for example by reference to the "Pesticide ‘

Manual", eleventh edition, 1997, published by the British Crop Protection Council. Of the compounds whose common names are not mentioned in the Pesticide Manual the full chemical names are as follows: trifloxystrobin - methyl (E.E)-methoxyimino-{2-[1-(3-trifluoromethylphenyl)- nL ethylideneaminooxymethyl]phenyl}acetate ’ spiroxamine - 8-tert-butyi-1,4-dioxaspiro[4.5)decan-2-yimethyi(ethyl)-

E ye, (propyl)amine do fenamidone - (S)-1-anilino-4-methyl-2-methylthio-4-phenylimidazolin-5-one Co EN 20 .

The composition of the invention may include for example a dispersing agent, emulsifying agent or wetting agent. Usually they are in the form of an aqueous B : concentrate. SE

The concentration of the active ingredient in the composition of the present invention, SE . as applied to plants is preferably within the range of 0.0001 to 1.0 per cent by weight, Co especially 0.0001 to 0.01 per cent by weight. In a primary‘composition, the amount of = oo : " active ingredient can vary widely and can be, for example, from 5 to 95 per cent by Co weight of the composition. . oo 30 a oo _ : : i

In the method of the invention the compound is generally applied to seeds, plants or oo their habitat. Thus, the compound can be applied directly to the soil before, at or after ) BE oo Co drilling so that the presence of active compound in the soil can control the growth of oo : fungi which may attack seeds. When the soil is treated directly the active compound ol can be applied in any manner which allows it to be intimately mixed with the soil such _

as by spraying, by broadcasting a solid form of granules, or by applying the active ingredient at the same time as drilling by inserting it in the same drill as the seeds. A suitable application rate is within the range of from 5 to 1000 g per hectare, more preferably from 10 to 500 g per hectare.

Alternatively the active compound can be applied directly to the plant by, for example, spraying or dusting either at the time when the fungus has begun to appear on the plant or before the appearance of fungus as a protective measure. In both such cases the preferred mode of application is by foliar spraying. It is generally important to obtain good control of fungi in the early stages of plant growth as this is the time when the plant can be most severely damaged. The spray or dust can conveniently contain a pre- or post-emergence herbicide if this is thought necessary. Sometimes, it is practicable to treat the roots of a plant before or during planting, for example, by dipping the roots in a suitable liquid or solid composition. When the active compound is applied directly to the plant a suitable rate of application is from 0.025 to 5 kg per hectare, preferably from 0.05 to 1 kg per hectare.

The compounds of formula | may be obtained by reacting an amine of formula |i v 0 .

EE SP) (

CH, with phosphoric or phosphorous acid. In general it is desirable to react an acid addition of salt of the compound of formula II, e.g. the hydrochloride, with a salt of the phosphorus acid, e.g. an alkali metal sait, such as the sodium salt.

This reaction can be carried out in aqueous solution

The invention is illustrated in the following Example.

Example 1

A solution of sodium phosphate dodecahydrate (8.8 g in water (75 ml)) was added to an aqueous solution of propy! 3-(dimethylamino)propylcarbamate hydrochloride (20 m} of concentration 776.9 g/l) in a further 75 ml of water. The mixture was stirred for 30 min, evaporated to dryness, dissolved in dichloromethane (200 ml) and the insoluble i ~ WO-01421626 ~ PCT/EP00/09360 C : : i . Co 5, . / . ho ¢ 5

RPE white solid (sodium chloride) filtered off . The filtrate was evaporated to leave dimethyi- [3-(propoxycarbonylamino)propyljammonium phosphate. as a viscous colourless oil.

Nmr spectroscopy confirmed that the product was a salt by observation of the chemical shifts relative to propyl 3-(dimethylamino)propylcarbamate.

Example 2

A solution of phosphorous acid (2.87 g in water (50 ml)) was stirred for 1 hour with a solution of sodium hydroxide (2.8 g in water (50 ml)). Propyl 3-(dimethylamino)propyi- carbamate hydrochloride (15.7 g) in water (50 ml) was added and the mixture stirred for 30 min, evaporated to dryness. dichloromethane (450 ml) added and re- evaporated. The residue was dissolved in dichloromethane (150 ml) allowed to stand for 1 hour and the insoluble white solid (sodium chloride) filtered off .The filtrate was evaporated to leave dimethyl-[3-(propoxycarbonylamino)propyllammonium phosphite, as a viscous colourless oil. ¢ . Nmr spectroscopy confirmed that the product was a salt by observation of the chemical

Ct yy shifts relative to propyl 3-(dimethylamino)propylcarbamate.

Fic oo

Claims

ey a PCT/EP00/09360 So h LEA (TH . CLAIMS -

1. A compound of formula . oo . : Pr . . 0 =i 0 a O-A* EN oo where X is hydrogen or O"A* and Ais a radical o oo NY N° NN N “0 ~~ : i»

2. A compound as claimed in claim 1, substantially as herein described and illustrated. .- : i : “3. A new compound, substantially as herein described. : :

~~. AMENDED SHEET Co A